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1,1-Dibromoethane → 2-Imino-3-(3-trifluoromethylphenyl)thiazolidine

HRID 22039
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 22039
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[S:11])[CH:6]=[CH:7][CH:8]=1.Br[CH:16](Br)[CH3:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[NH:12]=[C:10]1[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=2)[CH2:17][CH2:16][S:11]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 7358443-(Trifluoromethyl)phenylthiourea

Produkt 1

HCID 224169782-Imino-3-(3-trifluoromethylphenyl)thiazolidineAusbeute 110 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of N-(3-trifluoromethylphenyl)thiourea (6.1 g) , dibromoethane (5.7 g) and anhydrous potassium carbonate (11.5 g) in acetone (60 ml) was refluxed for 1 day. The solvent was removed by distillation therefrom, and the residue was extracted with ethyl ether, washed with water, dried over anhydrous magnesium sulfate and subjected to column chromatography to give 7.5 g of 2-imino-3-(3-trifluoromethylphenyl)thiazolidine. The thus obtained 2-imino-3- (3-trifluoromethylphenyl) thiazolidine (1.0 g), n-butyl chlorocarbonate (0.61 g) and triethylamine (1.2 g) were dissolved in tetrahydrofuran, and the resultant solution was stirred at room temperature for 5 hours. The solvent was removed, and the residue was extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was subjected to column chromatography to give 0.57 g of 2-butoxycarbonylimino-3- (3-trifluoromethylphenyl) thiazolidine.

Aufarbeitung

  1. customThe solvent was removed by distillation
  2. extractionthe residue was extracted with ethyl ether
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-53ae1588bcf846ae83835b473a226fb3
Quelldatensatz
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05426188

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